diff --git a/src/web/ng/Connection.hpp b/src/web/ng/Connection.hpp
index d9696dc6..309bb7d2 100644
--- a/src/web/ng/Connection.hpp
+++ b/src/web/ng/Connection.hpp
@@ -143,9 +143,9 @@ public:
      *
      * @param response The response to send.
      * @param yield The yield context.
-     * @return An error if the operation failed or nullopt if it succeeded.
+     * @return An error if the operation fails, otherwise nothing.
      */
-    virtual std::optional<Error>
+    virtual std::expected<void, Error>
     send(Response response, boost::asio::yield_context yield) = 0;
 
     /**
diff --git a/src/web/ng/Server.cpp b/src/web/ng/Server.cpp
index 53abd855..5726f1a8 100644
--- a/src/web/ng/Server.cpp
+++ b/src/web/ng/Server.cpp
@@ -147,9 +147,9 @@ makeConnection(
             tagDecoratorFactory
         );
         sslConnection->setTimeout(std::chrono::seconds{10});
-        auto const maybeError = sslConnection->sslHandshake(yield);
-        if (maybeError.has_value())
-            return std::unexpected{fmt::format("SSL handshake error: {}", maybeError->message())};
+        auto const expectedSuccess = sslConnection->sslHandshake(yield);
+        if (not expectedSuccess.has_value())
+            return std::unexpected{fmt::format("SSL handshake error: {}", expectedSuccess.error().message())};
 
         connection = std::move(sslConnection);
     } else {
diff --git a/src/web/ng/SubscriptionContext.cpp b/src/web/ng/SubscriptionContext.cpp
index 5cf07b6e..f3e76feb 100644
--- a/src/web/ng/SubscriptionContext.cpp
+++ b/src/web/ng/SubscriptionContext.cpp
@@ -70,8 +70,8 @@ SubscriptionContext::send(std::shared_ptr<std::string> message)
     }
 
     tasksGroup_.spawn(yield_, [this, message = std::move(message)](boost::asio::yield_context innerYield) mutable {
-        auto const maybeError = connection_.get().sendShared(std::move(message), innerYield);
-        if (maybeError.has_value() and errorHandler_(*maybeError, connection_)) {
+        auto const expectedSuccess = connection_.get().sendShared(std::move(message), innerYield);
+        if (not expectedSuccess.has_value() and errorHandler_(expectedSuccess.error(), connection_)) {
             connection_.get().close(innerYield);
             gotError_ = true;
         }
diff --git a/src/web/ng/impl/ConnectionHandler.cpp b/src/web/ng/impl/ConnectionHandler.cpp
index c8cdc6e1..d188f963 100644
--- a/src/web/ng/impl/ConnectionHandler.cpp
+++ b/src/web/ng/impl/ConnectionHandler.cpp
@@ -365,9 +365,9 @@ ConnectionHandler::processRequest(
     auto response = handleRequest(connection, subscriptionContext, request, yield);
 
     LOG(log_.trace()) << connection.tag() << "Sending response: " << response.message();
-    auto const maybeError = connection.send(std::move(response), yield);
-    if (maybeError.has_value()) {
-        return handleError(maybeError.value(), connection);
+    auto const expectedSuccess = connection.send(std::move(response), yield);
+    if (not expectedSuccess.has_value()) {
+        return handleError(expectedSuccess.error(), connection);
     }
     return std::nullopt;
 }
diff --git a/src/web/ng/impl/HttpConnection.hpp b/src/web/ng/impl/HttpConnection.hpp
index f64aa868..714284b2 100644
--- a/src/web/ng/impl/HttpConnection.hpp
+++ b/src/web/ng/impl/HttpConnection.hpp
@@ -62,7 +62,7 @@ public:
     virtual std::expected<ConnectionPtr, Error>
     upgrade(util::TagDecoratorFactory const& tagDecoratorFactory, boost::asio::yield_context yield) = 0;
 
-    virtual std::optional<Error>
+    virtual std::expected<void, Error>
     sendRaw(
         boost::beast::http::response<boost::beast::http::string_body> response,
         boost::asio::yield_context yield
@@ -123,7 +123,7 @@ public:
     HttpConnection&
     operator=(HttpConnection const& other) = delete;
 
-    std::optional<Error>
+    std::expected<void, Error>
     sslHandshake(boost::asio::yield_context yield)
         requires IsSslTcpStream<StreamType>
     {
@@ -132,11 +132,11 @@ public:
         auto const bytesUsed =
             stream_.async_handshake(boost::asio::ssl::stream_base::server, buffer_.cdata(), yield[error]);
         if (error)
-            return error;
+            return std::unexpected{error};
 
         buffer_.consume(bytesUsed);
 
-        return std::nullopt;
+        return {};
     }
 
     bool
@@ -145,7 +145,7 @@ public:
         return false;
     }
 
-    std::optional<Error>
+    std::expected<void, Error>
     sendRaw(
         boost::beast::http::response<boost::beast::http::string_body> response,
         boost::asio::yield_context yield
@@ -160,7 +160,7 @@ public:
         timeout_ = newTimeout;
     }
 
-    std::optional<Error>
+    std::expected<void, Error>
     send(Response response, boost::asio::yield_context yield) override
     {
         auto httpResponse = std::move(response).intoHttpResponse();
diff --git a/src/web/ng/impl/SendingQueue.hpp b/src/web/ng/impl/SendingQueue.hpp
index 4bd1a14d..2a1328c1 100644
--- a/src/web/ng/impl/SendingQueue.hpp
+++ b/src/web/ng/impl/SendingQueue.hpp
@@ -47,15 +47,15 @@ public:
     {
     }
 
-    std::optional<Error>
+    std::expected<void, Error>
     send(T message, boost::asio::yield_context yield)
     {
         if (error_)
-            return error_;
+            return std::unexpected{error_};
 
         queue_.push(std::move(message));
         if (isSending_)
-            return std::nullopt;
+            return {};
 
         isSending_ = true;
         while (not queue_.empty() and not error_) {
@@ -65,8 +65,8 @@ public:
         }
         isSending_ = false;
         if (error_)
-            return error_;
-        return std::nullopt;
+            return std::unexpected{error_};
+        return {};
     }
 };
 
diff --git a/src/web/ng/impl/WsConnection.hpp b/src/web/ng/impl/WsConnection.hpp
index bf1263e2..ad28b0d0 100644
--- a/src/web/ng/impl/WsConnection.hpp
+++ b/src/web/ng/impl/WsConnection.hpp
@@ -59,7 +59,7 @@ class WsConnectionBase : public Connection {
 public:
     using Connection::Connection;
 
-    virtual std::optional<Error>
+    virtual std::expected<void, Error>
     sendShared(std::shared_ptr<std::string> message, boost::asio::yield_context yield) = 0;
 };
 
@@ -108,14 +108,14 @@ public:
     WsConnection&
     operator=(WsConnection const&) = delete;
 
-    std::optional<Error>
+    std::expected<void, Error>
     performHandshake(boost::asio::yield_context yield)
     {
         Error error;
         stream_.async_accept(initialRequest_, yield[error]);
         if (error)
-            return error;
-        return std::nullopt;
+            return std::unexpected{error};
+        return {};
     }
 
     bool
@@ -124,7 +124,7 @@ public:
         return true;
     }
 
-    std::optional<Error>
+    std::expected<void, Error>
     sendShared(std::shared_ptr<std::string> message, boost::asio::yield_context yield) override
     {
         return sendingQueue_.send(std::move(message), yield);
@@ -140,7 +140,7 @@ public:
         stream_.set_option(wsTimeout);
     }
 
-    std::optional<Error>
+    std::expected<void, Error>
     send(Response response, boost::asio::yield_context yield) override
     {
         return sendingQueue_.send(std::move(response), yield);
@@ -206,9 +206,9 @@ makeWsConnection(
     auto connection = std::make_unique<WsConnection<StreamType>>(
         std::forward<StreamType>(stream), std::move(ip), std::move(buffer), std::move(request), tagDecoratorFactory
     );
-    auto maybeError = connection->performHandshake(yield);
-    if (maybeError.has_value())
-        return std::unexpected{maybeError.value()};
+    auto const expectedSuccess = connection->performHandshake(yield);
+    if (not expectedSuccess.has_value())
+        return std::unexpected{expectedSuccess.error()};
     return connection;
 }
 
diff --git a/tests/common/util/TestHttpClient.cpp b/tests/common/util/TestHttpClient.cpp
index ec233b11..189d0db0 100644
--- a/tests/common/util/TestHttpClient.cpp
+++ b/tests/common/util/TestHttpClient.cpp
@@ -186,7 +186,7 @@ HttpAsyncClient::HttpAsyncClient(boost::asio::io_context& ioContext) : stream_{i
 {
 }
 
-std::optional<boost::system::error_code>
+std::expected<void, boost::system::error_code>
 HttpAsyncClient::connect(
     std::string_view host,
     std::string_view port,
@@ -198,18 +198,18 @@ HttpAsyncClient::connect(
     boost::asio::ip::tcp::resolver resolver{stream_.get_executor()};
     auto const resolverResults = resolver.resolve(host, port, error);
     if (error)
-        return error;
+        return std::unexpected{error};
 
     ASSERT(!resolverResults.empty(), "No results from resolver");
 
     boost::beast::get_lowest_layer(stream_).expires_after(timeout);
     stream_.async_connect(resolverResults.begin()->endpoint(), yield[error]);
     if (error)
-        return error;
-    return std::nullopt;
+        return std::unexpected{error};
+    return {};
 }
 
-std::optional<boost::system::error_code>
+std::expected<void, boost::system::error_code>
 HttpAsyncClient::send(
     boost::beast::http::request<boost::beast::http::string_body> request,
     boost::asio::yield_context yield,
@@ -221,8 +221,8 @@ HttpAsyncClient::send(
     boost::beast::get_lowest_layer(stream_).expires_after(timeout);
     http::async_write(stream_, request, yield[error]);
     if (error)
-        return error;
-    return std::nullopt;
+        return std::unexpected{error};
+    return {};
 }
 
 std::expected<boost::beast::http::response<boost::beast::http::string_body>, boost::system::error_code>
diff --git a/tests/common/util/TestHttpClient.hpp b/tests/common/util/TestHttpClient.hpp
index 1816a8af..1079ed3b 100644
--- a/tests/common/util/TestHttpClient.hpp
+++ b/tests/common/util/TestHttpClient.hpp
@@ -78,7 +78,7 @@ class HttpAsyncClient {
 public:
     HttpAsyncClient(boost::asio::io_context& ioContext);
 
-    std::optional<boost::system::error_code>
+    std::expected<void, boost::system::error_code>
     connect(
         std::string_view host,
         std::string_view port,
@@ -86,7 +86,7 @@ public:
         std::chrono::steady_clock::duration timeout
     );
 
-    std::optional<boost::system::error_code>
+    std::expected<void, boost::system::error_code>
     send(
         boost::beast::http::request<boost::beast::http::string_body> request,
         boost::asio::yield_context yield,
@@ -98,6 +98,7 @@ public:
 
     void
     gracefulShutdown();
+
     void
     disconnect();
 };
diff --git a/tests/common/util/TestWebSocketClient.cpp b/tests/common/util/TestWebSocketClient.cpp
index 690c0a80..9985f787 100644
--- a/tests/common/util/TestWebSocketClient.cpp
+++ b/tests/common/util/TestWebSocketClient.cpp
@@ -137,7 +137,7 @@ WebSocketAsyncClient::WebSocketAsyncClient(boost::asio::io_context& ioContext) :
 {
 }
 
-std::optional<boost::system::error_code>
+std::expected<void, boost::system::error_code>
 WebSocketAsyncClient::connect(
     std::string const& host,
     std::string const& port,
@@ -153,7 +153,7 @@ WebSocketAsyncClient::connect(
     boost::beast::get_lowest_layer(stream_).expires_after(timeout);
     stream_.next_layer().async_connect(results, yield[error]);
     if (error)
-        return error;
+        return std::unexpected{error};
 
     boost::beast::websocket::stream_base::timeout wsTimeout =
         boost::beast::websocket::stream_base::timeout::suggested(boost::beast::role_type::client);
@@ -173,12 +173,12 @@ WebSocketAsyncClient::connect(
     stream_.async_handshake(fmt::format("{}:{}", host, port), "/", yield[error]);
 
     if (error)
-        return error;
+        return std::unexpected{error};
 
-    return std::nullopt;
+    return {};
 }
 
-std::optional<boost::system::error_code>
+std::expected<void, boost::system::error_code>
 WebSocketAsyncClient::send(
     boost::asio::yield_context yield,
     std::string_view message,
@@ -190,8 +190,8 @@ WebSocketAsyncClient::send(
     );
 
     if (error)
-        return error;
-    return std::nullopt;
+        return std::unexpected{error};
+    return {};
 }
 
 std::expected<std::string, boost::system::error_code>
diff --git a/tests/common/util/TestWebSocketClient.hpp b/tests/common/util/TestWebSocketClient.hpp
index c8ba064a..726574de 100644
--- a/tests/common/util/TestWebSocketClient.hpp
+++ b/tests/common/util/TestWebSocketClient.hpp
@@ -56,7 +56,7 @@ class WebSocketAsyncClient {
 public:
     WebSocketAsyncClient(boost::asio::io_context& ioContext);
 
-    std::optional<boost::system::error_code>
+    std::expected<void, boost::system::error_code>
     connect(
         std::string const& host,
         std::string const& port,
@@ -65,7 +65,7 @@ public:
         std::vector<WebHeader> additionalHeaders = {}
     );
 
-    std::optional<boost::system::error_code>
+    std::expected<void, boost::system::error_code>
     send(boost::asio::yield_context yield, std::string_view message, std::chrono::steady_clock::duration timeout);
 
     std::expected<std::string, boost::system::error_code>
diff --git a/tests/common/web/ng/MockConnection.hpp b/tests/common/web/ng/MockConnection.hpp
index 193e0922..85b1dbce 100644
--- a/tests/common/web/ng/MockConnection.hpp
+++ b/tests/common/web/ng/MockConnection.hpp
@@ -48,7 +48,7 @@ struct MockConnectionImpl : web::ng::Connection {
 
     MOCK_METHOD(void, setTimeout, (std::chrono::steady_clock::duration), (override));
 
-    using SendReturnType = std::optional<web::ng::Error>;
+    using SendReturnType = std::expected<void, web::ng::Error>;
     MOCK_METHOD(SendReturnType, send, (web::ng::Response, boost::asio::yield_context), (override));
 
     using ReceiveReturnType = std::expected<web::ng::Request, web::ng::Error>;
diff --git a/tests/common/web/ng/impl/MockHttpConnection.hpp b/tests/common/web/ng/impl/MockHttpConnection.hpp
index 7288a5f8..0d200ff4 100644
--- a/tests/common/web/ng/impl/MockHttpConnection.hpp
+++ b/tests/common/web/ng/impl/MockHttpConnection.hpp
@@ -44,7 +44,7 @@ struct MockHttpConnectionImpl : web::ng::impl::UpgradableConnection {
 
     MOCK_METHOD(void, setTimeout, (std::chrono::steady_clock::duration), (override));
 
-    using SendReturnType = std::optional<web::ng::Error>;
+    using SendReturnType = std::expected<void, web::ng::Error>;
     MOCK_METHOD(SendReturnType, send, (web::ng::Response, boost::asio::yield_context), (override));
 
     MOCK_METHOD(
diff --git a/tests/common/web/ng/impl/MockWsConnection.hpp b/tests/common/web/ng/impl/MockWsConnection.hpp
index 94445773..ee73158c 100644
--- a/tests/common/web/ng/impl/MockWsConnection.hpp
+++ b/tests/common/web/ng/impl/MockWsConnection.hpp
@@ -42,7 +42,7 @@ struct MockWsConnectionImpl : web::ng::impl::WsConnectionBase {
 
     MOCK_METHOD(void, setTimeout, (std::chrono::steady_clock::duration), (override));
 
-    using SendReturnType = std::optional<web::ng::Error>;
+    using SendReturnType = std::expected<void, web::ng::Error>;
     MOCK_METHOD(SendReturnType, send, (web::ng::Response, boost::asio::yield_context), (override));
 
     using ReceiveReturnType = std::expected<web::ng::Request, web::ng::Error>;
@@ -50,13 +50,7 @@ struct MockWsConnectionImpl : web::ng::impl::WsConnectionBase {
 
     MOCK_METHOD(void, close, (boost::asio::yield_context), (override));
 
-    using SendBufferReturnType = std::optional<web::ng::Error>;
-    MOCK_METHOD(
-        SendBufferReturnType,
-        sendShared,
-        (std::shared_ptr<std::string>, boost::asio::yield_context),
-        (override)
-    );
+    MOCK_METHOD(SendReturnType, sendShared, (std::shared_ptr<std::string>, boost::asio::yield_context), (override));
 };
 
 using MockWsConnection = testing::NiceMock<MockWsConnectionImpl>;
diff --git a/tests/unit/web/ng/ServerTests.cpp b/tests/unit/web/ng/ServerTests.cpp
index af83b3d9..2221c66c 100644
--- a/tests/unit/web/ng/ServerTests.cpp
+++ b/tests/unit/web/ng/ServerTests.cpp
@@ -261,9 +261,9 @@ TEST_F(ServerHttpTest, ClientDisconnects)
 {
     HttpAsyncClient client{ctx_};
     util::spawn(ctx_, [&](boost::asio::yield_context yield) {
-        auto maybeError =
+        auto expectedSuccess =
             client.connect("127.0.0.1", std::to_string(serverPort_), yield, std::chrono::milliseconds{100});
-        [&]() { ASSERT_FALSE(maybeError.has_value()) << maybeError->message(); }();
+        [&]() { ASSERT_TRUE(expectedSuccess.has_value()) << expectedSuccess.error().message(); }();
 
         client.disconnect();
         server_->stop(yield);
@@ -312,16 +312,17 @@ TEST_F(ServerHttpTest, OnConnectCheck)
                 return {};
             });
 
-        auto maybeError =
+        auto expectedSuccess =
             client.connect("127.0.0.1", std::to_string(serverPort), yield, std::chrono::milliseconds{100});
-        [&]() { ASSERT_FALSE(maybeError.has_value()) << maybeError->message(); }();
+        [&]() { ASSERT_TRUE(expectedSuccess.has_value()) << expectedSuccess.error().message(); }();
 
         // Have to send a request here because the server does async_detect_ssl() which waits for some data to appear
-        client.send(
+        expectedSuccess = client.send(
             http::request<http::string_body>{http::verb::get, "/", 11, requestMessage_},
             yield,
             std::chrono::milliseconds{100}
         );
+        [&]() { ASSERT_TRUE(expectedSuccess.has_value()) << expectedSuccess.error().message(); }();
 
         // Wait for the onConnectCheck to be called
         timer.expires_after(std::chrono::milliseconds{100});
@@ -374,16 +375,17 @@ TEST_F(ServerHttpTest, OnConnectCheckFailed)
     });
 
     util::spawn(ctx_, [&](boost::asio::yield_context yield) {
-        auto maybeError =
+        auto expectedSuccess =
             client.connect("127.0.0.1", std::to_string(serverPort), yield, std::chrono::milliseconds{100});
-        [&]() { ASSERT_FALSE(maybeError.has_value()) << maybeError->message(); }();
+        [&]() { ASSERT_TRUE(expectedSuccess.has_value()) << expectedSuccess.error().message(); }();
 
         // Have to send a request here because the server does async_detect_ssl() which waits for some data to appear
-        client.send(
+        expectedSuccess = client.send(
             http::request<http::string_body>{http::verb::get, "/", 11, requestMessage_},
             yield,
             std::chrono::milliseconds{100}
         );
+        [&]() { ASSERT_TRUE(expectedSuccess.has_value()) << expectedSuccess.error().message(); }();
 
         auto const response = client.receive(yield, std::chrono::milliseconds{100});
         [&]() { ASSERT_TRUE(response.has_value()) << response.error().message(); }();
@@ -434,15 +436,17 @@ TEST_F(ServerHttpTest, OnDisconnectHook)
 
         EXPECT_CALL(onDisconnectHookMock, Call).WillOnce([&timer](auto&&) { timer.cancel(); });
 
-        auto maybeError =
+        auto expectedSuccess =
             client.connect("127.0.0.1", std::to_string(serverPort), yield, std::chrono::milliseconds{100});
-        [&]() { ASSERT_FALSE(maybeError.has_value()) << maybeError->message(); }();
+        [&]() { ASSERT_TRUE(expectedSuccess.has_value()) << expectedSuccess.error().message(); }();
 
-        client.send(
+        // Have to send a request here because the server does async_detect_ssl() which waits for some data to appear
+        expectedSuccess = client.send(
             http::request<http::string_body>{http::verb::get, "/", 11, requestMessage_},
             yield,
             std::chrono::milliseconds{100}
         );
+        [&]() { ASSERT_TRUE(expectedSuccess.has_value()) << expectedSuccess.error().message(); }();
 
         client.gracefulShutdown();
 
@@ -463,17 +467,17 @@ TEST_F(ServerHttpTest, ClientIsDisconnectedIfServerStopped)
 {
     HttpAsyncClient client{ctx_};
     util::spawn(ctx_, [&](boost::asio::yield_context yield) {
-        auto maybeError =
+        auto expectedSuccess =
             client.connect("127.0.0.1", std::to_string(serverPort_), yield, std::chrono::milliseconds{100});
-        [&]() { ASSERT_FALSE(maybeError.has_value()) << maybeError->message(); }();
+        [&]() { ASSERT_TRUE(expectedSuccess.has_value()) << expectedSuccess.error().message(); }();
 
         // Have to send a request here because the server does async_detect_ssl() which waits for some data to appear
-        maybeError = client.send(
+        expectedSuccess = client.send(
             http::request<http::string_body>{http::verb::get, "/", 11, requestMessage_},
             yield,
             std::chrono::milliseconds{100}
         );
-        [&]() { ASSERT_FALSE(maybeError.has_value()) << maybeError->message(); }();
+        [&]() { ASSERT_TRUE(expectedSuccess.has_value()) << expectedSuccess.error().message(); }();
 
         auto message = client.receive(yield, std::chrono::milliseconds{100});
         EXPECT_TRUE(message.has_value()) << message.error().message();
@@ -498,13 +502,13 @@ TEST_P(ServerHttpTest, RequestResponse)
     Response const response{http::status::ok, "some response", Request{request}};
 
     util::spawn(ctx_, [&](boost::asio::yield_context yield) {
-        auto maybeError =
+        auto expectedSuccess =
             client.connect("127.0.0.1", std::to_string(serverPort_), yield, std::chrono::milliseconds{100});
-        [&]() { ASSERT_FALSE(maybeError.has_value()) << maybeError->message(); }();
+        [&]() { ASSERT_TRUE(expectedSuccess.has_value()) << expectedSuccess.error().message(); }();
 
         for ([[maybe_unused]] auto i : std::ranges::iota_view{0, 3}) {
-            maybeError = client.send(request, yield, std::chrono::milliseconds{100});
-            EXPECT_FALSE(maybeError.has_value()) << maybeError->message();
+            expectedSuccess = client.send(request, yield, std::chrono::milliseconds{100});
+            EXPECT_TRUE(expectedSuccess.has_value()) << expectedSuccess.error().message();
 
             auto const expectedResponse = client.receive(yield, std::chrono::milliseconds{100});
             [&]() { ASSERT_TRUE(expectedResponse.has_value()) << expectedResponse.error().message(); }();
@@ -548,9 +552,9 @@ TEST_F(ServerTest, WsClientDisconnects)
     WebSocketAsyncClient client{ctx_};
 
     util::spawn(ctx_, [&](boost::asio::yield_context yield) {
-        auto maybeError =
+        auto expectedSuccess =
             client.connect("127.0.0.1", std::to_string(serverPort_), yield, std::chrono::milliseconds{100});
-        [&]() { ASSERT_FALSE(maybeError.has_value()) << maybeError->message(); }();
+        [&]() { ASSERT_TRUE(expectedSuccess.has_value()) << expectedSuccess.error().message(); }();
 
         client.close();
         server_->stop(yield);
@@ -570,13 +574,13 @@ TEST_F(ServerTest, WsRequestResponse)
     Response const response{http::status::ok, "some response", Request{requestMessage_, headers}};
 
     util::spawn(ctx_, [&](boost::asio::yield_context yield) {
-        auto maybeError =
+        auto expectedSuccess =
             client.connect("127.0.0.1", std::to_string(serverPort_), yield, std::chrono::milliseconds{100});
-        [&]() { ASSERT_FALSE(maybeError.has_value()) << maybeError->message(); }();
+        [&]() { ASSERT_TRUE(expectedSuccess.has_value()) << expectedSuccess.error().message(); }();
 
         for ([[maybe_unused]] auto i : std::ranges::iota_view{0, 3}) {
-            maybeError = client.send(yield, requestMessage_, std::chrono::milliseconds{100});
-            EXPECT_FALSE(maybeError.has_value()) << maybeError->message();
+            expectedSuccess = client.send(yield, requestMessage_, std::chrono::milliseconds{100});
+            EXPECT_TRUE(expectedSuccess.has_value()) << expectedSuccess.error().message();
 
             auto const expectedResponse = client.receive(yield, std::chrono::milliseconds{100});
             [&]() { ASSERT_TRUE(expectedResponse.has_value()) << expectedResponse.error().message(); }();
@@ -608,10 +612,10 @@ TEST_F(ServerTest, WsClientIsDisconnectedIfServerStopped)
 {
     WebSocketAsyncClient client{ctx_};
     util::spawn(ctx_, [&](boost::asio::yield_context yield) {
-        auto maybeError =
+        auto expectedSuccess =
             client.connect("127.0.0.1", std::to_string(serverPort_), yield, std::chrono::milliseconds{100});
-        EXPECT_TRUE(maybeError.has_value());
-        EXPECT_EQ(maybeError.value().value(), static_cast<int>(boost::beast::websocket::error::upgrade_declined));
+        EXPECT_FALSE(expectedSuccess.has_value());
+        EXPECT_EQ(expectedSuccess.error().value(), static_cast<int>(boost::beast::websocket::error::upgrade_declined));
 
         ctx_.stop();
     });
diff --git a/tests/unit/web/ng/SubscriptionContextTests.cpp b/tests/unit/web/ng/SubscriptionContextTests.cpp
index 8d1061e1..285bce45 100644
--- a/tests/unit/web/ng/SubscriptionContextTests.cpp
+++ b/tests/unit/web/ng/SubscriptionContextTests.cpp
@@ -65,10 +65,13 @@ TEST_F(NgSubscriptionContextTests, Send)
         auto subscriptionContext = makeSubscriptionContext(yield);
         auto const message = std::make_shared<std::string>("some message");
 
-        EXPECT_CALL(connection_, sendShared).WillOnce([&message](std::shared_ptr<std::string> sendingMessage, auto&&) {
-            EXPECT_EQ(sendingMessage, message);
-            return std::nullopt;
-        });
+        EXPECT_CALL(connection_, sendShared)
+            .WillOnce(
+                [&message](std::shared_ptr<std::string> sendingMessage, auto&&) -> std::expected<void, web::ng::Error> {
+                    EXPECT_EQ(sendingMessage, message);
+                    return {};
+                }
+            );
         subscriptionContext.send(message);
         subscriptionContext.disconnect(yield);
     });
@@ -84,16 +87,24 @@ TEST_F(NgSubscriptionContextTests, SendOrder)
         testing::Sequence const sequence;
         EXPECT_CALL(connection_, sendShared)
             .InSequence(sequence)
-            .WillOnce([&message1](std::shared_ptr<std::string> sendingMessage, auto&&) {
-                EXPECT_EQ(sendingMessage, message1);
-                return std::nullopt;
-            });
+            .WillOnce(
+                [&message1](
+                    std::shared_ptr<std::string> sendingMessage, auto&&
+                ) -> std::expected<void, web::ng::Error> {
+                    EXPECT_EQ(sendingMessage, message1);
+                    return {};
+                }
+            );
         EXPECT_CALL(connection_, sendShared)
             .InSequence(sequence)
-            .WillOnce([&message2](std::shared_ptr<std::string> sendingMessage, auto&&) {
-                EXPECT_EQ(sendingMessage, message2);
-                return std::nullopt;
-            });
+            .WillOnce(
+                [&message2](
+                    std::shared_ptr<std::string> sendingMessage, auto&&
+                ) -> std::expected<void, web::ng::Error> {
+                    EXPECT_EQ(sendingMessage, message2);
+                    return {};
+                }
+            );
 
         subscriptionContext.send(message1);
         subscriptionContext.send(message2);
@@ -109,7 +120,7 @@ TEST_F(NgSubscriptionContextTests, SendFailed)
 
         EXPECT_CALL(connection_, sendShared).WillOnce([&message](std::shared_ptr<std::string> sendingMessage, auto&&) {
             EXPECT_EQ(sendingMessage, message);
-            return boost::system::errc::make_error_code(boost::system::errc::not_supported);
+            return std::unexpected{boost::system::errc::make_error_code(boost::system::errc::not_supported)};
         });
         EXPECT_CALL(errorHandler_, Call).WillOnce(testing::Return(true));
         EXPECT_CALL(connection_, close);
@@ -125,11 +136,15 @@ TEST_F(NgSubscriptionContextTests, SendTooManySubscriptions)
         auto const message = std::make_shared<std::string>("message1");
 
         EXPECT_CALL(connection_, sendShared)
-            .WillOnce([&message](std::shared_ptr<std::string> sendingMessage, boost::asio::yield_context innerYield) {
-                boost::asio::post(innerYield);  // simulate send is slow by switching to another coroutine
-                EXPECT_EQ(sendingMessage, message);
-                return std::nullopt;
-            });
+            .WillOnce(
+                [&message](
+                    std::shared_ptr<std::string> sendingMessage, boost::asio::yield_context innerYield
+                ) -> std::expected<void, web::ng::Error> {
+                    boost::asio::post(innerYield);  // simulate send is slow by switching to another coroutine
+                    EXPECT_EQ(sendingMessage, message);
+                    return {};
+                }
+            );
         EXPECT_CALL(connection_, close);
 
         subscriptionContext.send(message);
diff --git a/tests/unit/web/ng/impl/ConnectionHandlerTests.cpp b/tests/unit/web/ng/impl/ConnectionHandlerTests.cpp
index 2dfcce9e..f944abc5 100644
--- a/tests/unit/web/ng/impl/ConnectionHandlerTests.cpp
+++ b/tests/unit/web/ng/impl/ConnectionHandlerTests.cpp
@@ -173,10 +173,11 @@ TEST_F(ConnectionHandlerSequentialProcessingTest, Receive_Handle_NoHandler_Send)
         .WillOnce(Return(makeRequest("some_request", headers)))
         .WillOnce(Return(makeError(websocket::error::closed)));
 
-    EXPECT_CALL(*mockHttpConnection, send).WillOnce([](Response response, auto&&) {
-        EXPECT_EQ(response.message(), "WebSocket is not supported by this server");
-        return std::nullopt;
-    });
+    EXPECT_CALL(*mockHttpConnection, send)
+        .WillOnce([](Response response, auto&&) -> std::expected<void, web::ng::Error> {
+            EXPECT_EQ(response.message(), "WebSocket is not supported by this server");
+            return {};
+        });
 
     EXPECT_CALL(onDisconnectMock, Call).WillOnce([connectionPtr = mockHttpConnection.get()](Connection const& c) {
         EXPECT_EQ(&c, connectionPtr);
@@ -197,13 +198,14 @@ TEST_F(ConnectionHandlerSequentialProcessingTest, Receive_Handle_BadTarget_Send)
         .WillOnce(Return(makeRequest(http::request<http::string_body>{http::verb::get, target, 11, requestMessage})))
         .WillOnce(Return(makeError(http::error::end_of_stream)));
 
-    EXPECT_CALL(*mockHttpConnection, send).WillOnce([](Response response, auto&&) {
-        EXPECT_EQ(response.message(), "Bad target");
-        auto const httpResponse = std::move(response).intoHttpResponse();
-        EXPECT_EQ(httpResponse.result(), http::status::bad_request);
-        EXPECT_EQ(httpResponse.version(), 11);
-        return std::nullopt;
-    });
+    EXPECT_CALL(*mockHttpConnection, send)
+        .WillOnce([](Response response, auto&&) -> std::expected<void, web::ng::Error> {
+            EXPECT_EQ(response.message(), "Bad target");
+            auto const httpResponse = std::move(response).intoHttpResponse();
+            EXPECT_EQ(httpResponse.result(), http::status::bad_request);
+            EXPECT_EQ(httpResponse.version(), 11);
+            return {};
+        });
 
     EXPECT_CALL(onDisconnectMock, Call).WillOnce([connectionPtr = mockHttpConnection.get()](Connection const& c) {
         EXPECT_EQ(&c, connectionPtr);
@@ -221,10 +223,11 @@ TEST_F(ConnectionHandlerSequentialProcessingTest, Receive_Handle_BadMethod_Send)
         .WillOnce(Return(makeRequest(http::request<http::string_body>{http::verb::acl, "/", 11})))
         .WillOnce(Return(makeError(http::error::end_of_stream)));
 
-    EXPECT_CALL(*mockHttpConnection, send).WillOnce([](Response response, auto&&) {
-        EXPECT_EQ(response.message(), "Unsupported http method");
-        return std::nullopt;
-    });
+    EXPECT_CALL(*mockHttpConnection, send)
+        .WillOnce([](Response response, auto&&) -> std::expected<void, web::ng::Error> {
+            EXPECT_EQ(response.message(), "Unsupported http method");
+            return {};
+        });
 
     EXPECT_CALL(onDisconnectMock, Call).WillOnce([connectionPtr = mockHttpConnection.get()](Connection const& c) {
         EXPECT_EQ(&c, connectionPtr);
@@ -255,10 +258,11 @@ TEST_F(ConnectionHandlerSequentialProcessingTest, Receive_Handle_Send)
         return Response(http::status::ok, responseMessage, request);
     });
 
-    EXPECT_CALL(*mockWsConnection, send).WillOnce([&responseMessage](Response response, auto&&) {
-        EXPECT_EQ(response.message(), responseMessage);
-        return std::nullopt;
-    });
+    EXPECT_CALL(*mockWsConnection, send)
+        .WillOnce([&responseMessage](Response response, auto&&) -> std::expected<void, web::ng::Error> {
+            EXPECT_EQ(response.message(), responseMessage);
+            return {};
+        });
 
     EXPECT_CALL(onDisconnectMock, Call).WillOnce([connectionPtr = mockWsConnection.get()](Connection const& c) {
         EXPECT_EQ(&c, connectionPtr);
@@ -290,13 +294,17 @@ TEST_F(ConnectionHandlerSequentialProcessingTest, SendSubscriptionMessage)
             return Response(http::status::ok, "", request);
         });
 
-    EXPECT_CALL(*mockWsConnection, send).WillOnce(Return(std::nullopt));
+    EXPECT_CALL(*mockWsConnection, send).WillOnce(Return(std::expected<void, web::ng::Error>{}));
 
     EXPECT_CALL(*mockWsConnection, sendShared)
-        .WillOnce([&subscriptionMessage](std::shared_ptr<std::string> sendingMessage, auto&&) {
-            EXPECT_EQ(*sendingMessage, subscriptionMessage);
-            return std::nullopt;
-        });
+        .WillOnce(
+            [&subscriptionMessage](
+                std::shared_ptr<std::string> sendingMessage, auto&&
+            ) -> std::expected<void, web::ng::Error> {
+                EXPECT_EQ(*sendingMessage, subscriptionMessage);
+                return {};
+            }
+        );
 
     EXPECT_CALL(onDisconnectMock, Call).WillOnce([connectionPtr = mockWsConnection.get()](Connection const& c) {
         EXPECT_EQ(&c, connectionPtr);
@@ -328,7 +336,7 @@ TEST_F(ConnectionHandlerSequentialProcessingTest, SubscriptionContextIsDisconnec
             return Response(http::status::ok, "", request);
         });
 
-    EXPECT_CALL(*mockWsConnection, send).WillOnce(Return(std::nullopt));
+    EXPECT_CALL(*mockWsConnection, send).WillOnce(Return(std::expected<void, web::ng::Error>{}));
 
     EXPECT_CALL(onDisconnectHook, Call).After(expectationReceiveCalled);
 
@@ -367,10 +375,11 @@ TEST_F(ConnectionHandlerSequentialProcessingTest, SubscriptionContextIsNullForHt
             return Response(http::status::ok, responseMessage, request);
         });
 
-    EXPECT_CALL(*mockHttpConnection, send).WillOnce([&responseMessage](Response response, auto&&) {
-        EXPECT_EQ(response.message(), responseMessage);
-        return std::nullopt;
-    });
+    EXPECT_CALL(*mockHttpConnection, send)
+        .WillOnce([&responseMessage](Response response, auto&&) -> std::expected<void, web::ng::Error> {
+            EXPECT_EQ(response.message(), responseMessage);
+            return {};
+        });
 
     EXPECT_CALL(
         *mockHttpConnection,
@@ -413,10 +422,12 @@ TEST_F(ConnectionHandlerSequentialProcessingTest, Receive_Handle_Send_Loop)
         return Response(http::status::ok, responseMessage, request);
     });
 
-    EXPECT_CALL(*mockHttpConnection, send).Times(3).WillRepeatedly([&responseMessage](Response response, auto&&) {
-        EXPECT_EQ(response.message(), responseMessage);
-        return std::nullopt;
-    });
+    EXPECT_CALL(*mockHttpConnection, send)
+        .Times(3)
+        .WillRepeatedly([&responseMessage](Response response, auto&&) -> std::expected<void, web::ng::Error> {
+            EXPECT_EQ(response.message(), responseMessage);
+            return {};
+        });
 
     EXPECT_CALL(
         *mockHttpConnection,
@@ -456,7 +467,7 @@ TEST_F(ConnectionHandlerSequentialProcessingTest, Receive_Handle_SendError)
 
     EXPECT_CALL(*mockHttpConnection, send).WillOnce([&responseMessage](Response response, auto&&) {
         EXPECT_EQ(response.message(), responseMessage);
-        return makeError(http::error::end_of_stream).error();
+        return makeError(http::error::end_of_stream);
     });
 
     EXPECT_CALL(onDisconnectMock, Call).WillOnce([connectionPtr = mockHttpConnection.get()](Connection const& c) {
@@ -498,7 +509,7 @@ TEST_F(ConnectionHandlerSequentialProcessingTest, OnIpChangeHookCalledWhenSentFr
 
     EXPECT_CALL(*mockHttpConnectionFromProxy, send).WillOnce([&responseMessage](Response response, auto&&) {
         EXPECT_EQ(response.message(), responseMessage);
-        return makeError(http::error::end_of_stream).error();
+        return makeError(http::error::end_of_stream);
     });
 
     EXPECT_CALL(onDisconnectMock, Call)
@@ -542,12 +553,12 @@ TEST_F(ConnectionHandlerSequentialProcessingTest, Stop)
         send(testing::ResultOf([](Response const& r) { return r.message(); }, responseMessage), testing::_)
     )
         .Times(3)
-        .WillRepeatedly([&](auto&&, auto&&) {
+        .WillRepeatedly([&](auto&&, auto&&) -> std::expected<void, web::ng::Error> {
             ++numCalls;
             if (numCalls == 3)
                 util::spawn(ctx_, [this](auto yield) { connectionHandler.stop(yield); });
 
-            return std::nullopt;
+            return {};
         });
 
     EXPECT_CALL(
@@ -659,10 +670,11 @@ TEST_F(ConnectionHandlerParallelProcessingTest, Receive_Handle_Send)
         return Response(http::status::ok, responseMessage, request);
     });
 
-    EXPECT_CALL(*mockWsConnection, send).WillOnce([&responseMessage](Response response, auto&&) {
-        EXPECT_EQ(response.message(), responseMessage);
-        return std::nullopt;
-    });
+    EXPECT_CALL(*mockWsConnection, send)
+        .WillOnce([&responseMessage](Response response, auto&&) -> std::expected<void, web::ng::Error> {
+            EXPECT_EQ(response.message(), responseMessage);
+            return {};
+        });
 
     EXPECT_CALL(onDisconnectMock, Call).WillOnce([connectionPtr = mockWsConnection.get()](Connection const& c) {
         EXPECT_EQ(&c, connectionPtr);
@@ -699,10 +711,11 @@ TEST_F(ConnectionHandlerParallelProcessingTest, OnIpChangeHookCalledWhenSentFrom
         return Response(http::status::ok, responseMessage, request);
     });
 
-    EXPECT_CALL(*mockWsConnectionFromProxy, send).WillOnce([&responseMessage](Response response, auto&&) {
-        EXPECT_EQ(response.message(), responseMessage);
-        return std::nullopt;
-    });
+    EXPECT_CALL(*mockWsConnectionFromProxy, send)
+        .WillOnce([&responseMessage](Response response, auto&&) -> std::expected<void, web::ng::Error> {
+            EXPECT_EQ(response.message(), responseMessage);
+            return {};
+        });
 
     EXPECT_CALL(onDisconnectMock, Call)
         .WillOnce([this, connectionPtr = mockWsConnectionFromProxy.get()](Connection const& c) {
@@ -738,10 +751,12 @@ TEST_F(ConnectionHandlerParallelProcessingTest, Receive_Handle_Send_Loop)
         return Response(http::status::ok, responseMessage, request);
     });
 
-    EXPECT_CALL(*mockWsConnection, send).Times(2).WillRepeatedly([&responseMessage](Response response, auto&&) {
-        EXPECT_EQ(response.message(), responseMessage);
-        return std::nullopt;
-    });
+    EXPECT_CALL(*mockWsConnection, send)
+        .Times(2)
+        .WillRepeatedly([&responseMessage](Response response, auto&&) -> std::expected<void, web::ng::Error> {
+            EXPECT_EQ(response.message(), responseMessage);
+            return {};
+        });
 
     EXPECT_CALL(onDisconnectMock, Call).WillOnce([connectionPtr = mockWsConnection.get()](Connection const& c) {
         EXPECT_EQ(&c, connectionPtr);
@@ -787,7 +802,7 @@ TEST_F(ConnectionHandlerParallelProcessingTest, Receive_Handle_Send_Loop_TooMany
         send(testing::ResultOf([](Response response) { return response.message(); }, responseMessage), testing::_)
     )
         .Times(3)
-        .WillRepeatedly(Return(std::nullopt));
+        .WillRepeatedly(Return(std::expected<void, web::ng::Error>{}));
 
     EXPECT_CALL(
         *mockWsConnection,
@@ -799,7 +814,7 @@ TEST_F(ConnectionHandlerParallelProcessingTest, Receive_Handle_Send_Loop_TooMany
         )
     )
         .Times(2)
-        .WillRepeatedly(Return(std::nullopt));
+        .WillRepeatedly(Return(std::expected<void, web::ng::Error>{}));
 
     EXPECT_CALL(onDisconnectMock, Call).WillOnce([connectionPtr = mockWsConnection.get()](Connection const& c) {
         EXPECT_EQ(&c, connectionPtr);
diff --git a/tests/unit/web/ng/impl/HttpConnectionTests.cpp b/tests/unit/web/ng/impl/HttpConnectionTests.cpp
index 1b5eae38..ee2f24a0 100644
--- a/tests/unit/web/ng/impl/HttpConnectionTests.cpp
+++ b/tests/unit/web/ng/impl/HttpConnectionTests.cpp
@@ -80,8 +80,9 @@ protected:
 TEST_F(HttpConnectionTests, wasUpgraded)
 {
     util::spawn(ctx_, [this](boost::asio::yield_context yield) {
-        auto maybeError = httpClient_.connect("localhost", httpServer_.port(), yield, std::chrono::milliseconds{100});
-        [&]() { ASSERT_FALSE(maybeError.has_value()) << maybeError->message(); }();
+        auto expectedSuccess =
+            httpClient_.connect("localhost", httpServer_.port(), yield, std::chrono::milliseconds{100});
+        [&]() { ASSERT_TRUE(expectedSuccess.has_value()) << expectedSuccess.error().message(); }();
     });
 
     runSpawn([this](boost::asio::yield_context yield) {
@@ -95,11 +96,12 @@ TEST_F(HttpConnectionTests, Receive)
     request_.set(boost::beast::http::field::user_agent, "test_client");
 
     util::spawn(ctx_, [this](boost::asio::yield_context yield) {
-        auto maybeError = httpClient_.connect("localhost", httpServer_.port(), yield, std::chrono::milliseconds{100});
-        [&]() { ASSERT_FALSE(maybeError.has_value()) << maybeError->message(); }();
+        auto expectedSuccess =
+            httpClient_.connect("localhost", httpServer_.port(), yield, std::chrono::milliseconds{100});
+        [&]() { ASSERT_TRUE(expectedSuccess.has_value()) << expectedSuccess.error().message(); }();
 
-        maybeError = httpClient_.send(request_, yield, std::chrono::milliseconds{100});
-        [&]() { ASSERT_FALSE(maybeError.has_value()) << maybeError->message(); }();
+        expectedSuccess = httpClient_.send(request_, yield, std::chrono::milliseconds{100});
+        [&]() { ASSERT_TRUE(expectedSuccess.has_value()) << expectedSuccess.error().message(); }();
     });
 
     runSpawn([this](boost::asio::yield_context yield) {
@@ -123,8 +125,9 @@ TEST_F(HttpConnectionTests, Receive)
 TEST_F(HttpConnectionTests, ReceiveTimeout)
 {
     util::spawn(ctx_, [this](boost::asio::yield_context yield) {
-        auto maybeError = httpClient_.connect("localhost", httpServer_.port(), yield, std::chrono::milliseconds{1});
-        [&]() { ASSERT_FALSE(maybeError.has_value()) << maybeError->message(); }();
+        auto expectedSuccess =
+            httpClient_.connect("localhost", httpServer_.port(), yield, std::chrono::milliseconds{1});
+        [&]() { ASSERT_TRUE(expectedSuccess.has_value()) << expectedSuccess.error().message(); }();
     });
 
     runSpawn([this](boost::asio::yield_context yield) {
@@ -138,8 +141,9 @@ TEST_F(HttpConnectionTests, ReceiveTimeout)
 TEST_F(HttpConnectionTests, ReceiveClientDisconnected)
 {
     util::spawn(ctx_, [this](boost::asio::yield_context yield) {
-        auto maybeError = httpClient_.connect("localhost", httpServer_.port(), yield, std::chrono::milliseconds{1});
-        [&]() { ASSERT_FALSE(maybeError.has_value()) << maybeError->message(); }();
+        auto expectedSuccess =
+            httpClient_.connect("localhost", httpServer_.port(), yield, std::chrono::milliseconds{1});
+        [&]() { ASSERT_TRUE(expectedSuccess.has_value()) << expectedSuccess.error().message(); }();
         httpClient_.disconnect();
     });
 
@@ -157,11 +161,12 @@ TEST_F(HttpConnectionTests, Send)
     Response const response{http::status::ok, "some response data", request};
 
     util::spawn(ctx_, [this, response = response](boost::asio::yield_context yield) mutable {
-        auto maybeError = httpClient_.connect("localhost", httpServer_.port(), yield, std::chrono::milliseconds{100});
-        [&]() { ASSERT_FALSE(maybeError.has_value()) << maybeError->message(); }();
+        auto expectedSuccess =
+            httpClient_.connect("localhost", httpServer_.port(), yield, std::chrono::milliseconds{100});
+        [&]() { ASSERT_TRUE(expectedSuccess.has_value()) << expectedSuccess.error().message(); }();
 
         auto const expectedResponse = httpClient_.receive(yield, std::chrono::milliseconds{100});
-        [&]() { ASSERT_TRUE(expectedResponse.has_value()) << maybeError->message(); }();
+        [&]() { ASSERT_TRUE(expectedResponse.has_value()) << expectedResponse.error().message(); }();
 
         auto const receivedResponse = expectedResponse.value();
         auto const sentResponse = std::move(response).intoHttpResponse();
@@ -173,8 +178,8 @@ TEST_F(HttpConnectionTests, Send)
 
     runSpawn([this, &response](boost::asio::yield_context yield) {
         auto connection = acceptConnection(yield);
-        auto maybeError = connection->send(response, yield);
-        [&]() { ASSERT_FALSE(maybeError.has_value()) << maybeError->message(); }();
+        auto expectedSuccess = connection->send(response, yield);
+        [&]() { ASSERT_TRUE(expectedSuccess.has_value()) << expectedSuccess.error().message(); }();
     });
 }
 
@@ -184,8 +189,9 @@ TEST_F(HttpConnectionTests, SendMultipleTimes)
     Response const response{http::status::ok, "some response data", request};
 
     util::spawn(ctx_, [this, response = response](boost::asio::yield_context yield) mutable {
-        auto maybeError = httpClient_.connect("localhost", httpServer_.port(), yield, std::chrono::milliseconds{100});
-        [&]() { ASSERT_FALSE(maybeError.has_value()) << maybeError->message(); }();
+        auto expectedSuccess =
+            httpClient_.connect("localhost", httpServer_.port(), yield, std::chrono::milliseconds{100});
+        [&]() { ASSERT_TRUE(expectedSuccess.has_value()) << expectedSuccess.error().message(); }();
 
         for ([[maybe_unused]] auto i : std::ranges::iota_view{0, 3}) {
             auto const expectedResponse = httpClient_.receive(yield, std::chrono::milliseconds{100});
@@ -204,8 +210,8 @@ TEST_F(HttpConnectionTests, SendMultipleTimes)
         auto connection = acceptConnection(yield);
 
         for ([[maybe_unused]] auto i : std::ranges::iota_view{0, 3}) {
-            auto maybeError = connection->send(response, yield);
-            [&]() { ASSERT_FALSE(maybeError.has_value()) << maybeError->message(); }();
+            auto expectedSuccess = connection->send(response, yield);
+            [&]() { ASSERT_TRUE(expectedSuccess.has_value()) << expectedSuccess.error().message(); }();
         }
     });
 }
@@ -216,9 +222,9 @@ TEST_F(HttpConnectionTests, SendMultipleTimesFromMultipleCoroutines)
     Response const response{http::status::ok, "some response data", request};
 
     util::spawn(ctx_, [this, response = response](boost::asio::yield_context yield) mutable {
-        auto const maybeError =
+        auto const expectedSuccess =
             httpClient_.connect("localhost", httpServer_.port(), yield, std::chrono::milliseconds{100});
-        [&]() { ASSERT_FALSE(maybeError.has_value()) << maybeError->message(); }();
+        [&]() { ASSERT_TRUE(expectedSuccess.has_value()) << expectedSuccess.error().message(); }();
 
         for ([[maybe_unused]] auto i : std::ranges::iota_view{0, 3}) {
             auto const expectedResponse = httpClient_.receive(yield, std::chrono::milliseconds{100});
@@ -239,8 +245,8 @@ TEST_F(HttpConnectionTests, SendMultipleTimesFromMultipleCoroutines)
         util::CoroutineGroup group{yield};
         for ([[maybe_unused]] auto i : std::ranges::iota_view{0, 3}) {
             group.spawn(yield, [&response, &connection](boost::asio::yield_context innerYield) {
-                auto const maybeError = connection->send(response, innerYield);
-                [&]() { ASSERT_FALSE(maybeError.has_value()) << maybeError->message(); }();
+                auto const expectedSuccess = connection->send(response, innerYield);
+                [&]() { ASSERT_TRUE(expectedSuccess.has_value()) << expectedSuccess.error().message(); }();
             });
         }
         group.asyncWait(yield);
@@ -251,9 +257,9 @@ TEST_F(HttpConnectionTests, SendMultipleTimesClientDisconnected)
 {
     Response const response{http::status::ok, "some response data", Request{request_}};
     util::spawn(ctx_, [this, response = response](boost::asio::yield_context yield) mutable {
-        auto const maybeError =
+        auto const expectedSuccess =
             httpClient_.connect("localhost", httpServer_.port(), yield, std::chrono::milliseconds{1});
-        [&]() { ASSERT_FALSE(maybeError.has_value()) << maybeError->message(); }();
+        [&]() { ASSERT_TRUE(expectedSuccess.has_value()) << expectedSuccess.error().message(); }();
         auto const expectedResponse = httpClient_.receive(yield, std::chrono::milliseconds{100});
         [&]() { ASSERT_TRUE(expectedResponse.has_value()) << expectedResponse.error().message(); }();
         httpClient_.disconnect();
@@ -262,15 +268,15 @@ TEST_F(HttpConnectionTests, SendMultipleTimesClientDisconnected)
     runSpawn([this, &response](boost::asio::yield_context yield) {
         auto connection = acceptConnection(yield);
         connection->setTimeout(std::chrono::milliseconds{1});
-        auto maybeError = connection->send(response, yield);
+        auto expectedSuccess = connection->send(response, yield);
         size_t counter{1};
-        while (not maybeError.has_value() and counter < 100) {
+        while (expectedSuccess.has_value() and counter < 100) {
             ++counter;
-            maybeError = connection->send(response, yield);
+            expectedSuccess = connection->send(response, yield);
         }
         // Sending after getting an error should be safe
-        maybeError = connection->send(response, yield);
-        EXPECT_TRUE(maybeError.has_value());
+        expectedSuccess = connection->send(response, yield);
+        EXPECT_FALSE(expectedSuccess.has_value());
         EXPECT_LT(counter, 100);
     });
 }
@@ -279,20 +285,21 @@ TEST_F(HttpConnectionTests, SendClientDisconnected)
 {
     Response const response{http::status::ok, "some response data", Request{request_}};
     util::spawn(ctx_, [this, response = response](boost::asio::yield_context yield) mutable {
-        auto maybeError = httpClient_.connect("localhost", httpServer_.port(), yield, std::chrono::milliseconds{1});
-        [&]() { ASSERT_FALSE(maybeError.has_value()) << maybeError->message(); }();
+        auto expectedSuccess =
+            httpClient_.connect("localhost", httpServer_.port(), yield, std::chrono::milliseconds{1});
+        [&]() { ASSERT_TRUE(expectedSuccess.has_value()) << expectedSuccess.error().message(); }();
         httpClient_.disconnect();
     });
     runSpawn([this, &response](boost::asio::yield_context yield) {
         auto connection = acceptConnection(yield);
         connection->setTimeout(std::chrono::milliseconds{1});
-        auto maybeError = connection->send(response, yield);
+        auto expectedSuccess = connection->send(response, yield);
         size_t counter{1};
-        while (not maybeError.has_value() and counter < 100) {
+        while (expectedSuccess.has_value() and counter < 100) {
             ++counter;
-            maybeError = connection->send(response, yield);
+            expectedSuccess = connection->send(response, yield);
         }
-        EXPECT_TRUE(maybeError.has_value());
+        EXPECT_FALSE(expectedSuccess.has_value());
         EXPECT_LT(counter, 100);
     });
 }
@@ -300,15 +307,16 @@ TEST_F(HttpConnectionTests, SendClientDisconnected)
 TEST_F(HttpConnectionTests, Close)
 {
     util::spawn(ctx_, [this](boost::asio::yield_context yield) {
-        auto maybeError = httpClient_.connect("localhost", httpServer_.port(), yield, std::chrono::milliseconds{100});
-        [&]() { ASSERT_FALSE(maybeError.has_value()) << maybeError->message(); }();
+        auto expectedSuccess =
+            httpClient_.connect("localhost", httpServer_.port(), yield, std::chrono::milliseconds{100});
+        [&]() { ASSERT_TRUE(expectedSuccess.has_value()) << expectedSuccess.error().message(); }();
 
         size_t counter{0};
-        while (not maybeError.has_value() and counter < 100) {
+        while (expectedSuccess.has_value() and counter < 100) {
             ++counter;
-            maybeError = httpClient_.send(request_, yield, std::chrono::milliseconds{1});
+            expectedSuccess = httpClient_.send(request_, yield, std::chrono::milliseconds{1});
         }
-        EXPECT_TRUE(maybeError.has_value());
+        EXPECT_FALSE(expectedSuccess.has_value());
         EXPECT_LT(counter, 100);
     });
 
@@ -322,11 +330,12 @@ TEST_F(HttpConnectionTests, Close)
 TEST_F(HttpConnectionTests, IsUpgradeRequested_GotHttpRequest)
 {
     util::spawn(ctx_, [this](boost::asio::yield_context yield) {
-        auto maybeError = httpClient_.connect("localhost", httpServer_.port(), yield, std::chrono::milliseconds{100});
-        [&]() { ASSERT_FALSE(maybeError.has_value()) << maybeError->message(); }();
+        auto expectedSuccess =
+            httpClient_.connect("localhost", httpServer_.port(), yield, std::chrono::milliseconds{100});
+        [&]() { ASSERT_TRUE(expectedSuccess.has_value()) << expectedSuccess.error().message(); }();
 
-        maybeError = httpClient_.send(request_, yield, std::chrono::milliseconds{1});
-        EXPECT_FALSE(maybeError.has_value()) << maybeError->message();
+        expectedSuccess = httpClient_.send(request_, yield, std::chrono::milliseconds{1});
+        EXPECT_TRUE(expectedSuccess.has_value()) << expectedSuccess.error().message();
     });
 
     runSpawn([this](boost::asio::yield_context yield) {
@@ -340,8 +349,9 @@ TEST_F(HttpConnectionTests, IsUpgradeRequested_GotHttpRequest)
 TEST_F(HttpConnectionTests, IsUpgradeRequested_FailedToFetch)
 {
     util::spawn(ctx_, [this](boost::asio::yield_context yield) {
-        auto maybeError = httpClient_.connect("localhost", httpServer_.port(), yield, std::chrono::milliseconds{100});
-        [&]() { ASSERT_FALSE(maybeError.has_value()) << maybeError->message(); }();
+        auto expectedSuccess =
+            httpClient_.connect("localhost", httpServer_.port(), yield, std::chrono::milliseconds{100});
+        [&]() { ASSERT_TRUE(expectedSuccess.has_value()) << expectedSuccess.error().message(); }();
     });
 
     runSpawn([this](boost::asio::yield_context yield) {
@@ -357,8 +367,8 @@ TEST_F(HttpConnectionTests, Upgrade)
     WebSocketAsyncClient wsClient{ctx_};
 
     util::spawn(ctx_, [this, &wsClient](boost::asio::yield_context yield) {
-        auto maybeError = wsClient.connect("localhost", httpServer_.port(), yield, std::chrono::milliseconds{100});
-        [&]() { ASSERT_FALSE(maybeError.has_value()) << maybeError->message(); }();
+        auto expectedSuccess = wsClient.connect("localhost", httpServer_.port(), yield, std::chrono::milliseconds{100});
+        [&]() { ASSERT_TRUE(expectedSuccess.has_value()) << expectedSuccess.error().message(); }();
     });
 
     runSpawn([this](boost::asio::yield_context yield) {
@@ -375,8 +385,9 @@ TEST_F(HttpConnectionTests, Upgrade)
 TEST_F(HttpConnectionTests, Ip)
 {
     util::spawn(ctx_, [this](boost::asio::yield_context yield) mutable {
-        auto maybeError = httpClient_.connect("localhost", httpServer_.port(), yield, std::chrono::milliseconds{100});
-        [&]() { ASSERT_FALSE(maybeError.has_value()) << maybeError->message(); }();
+        auto expectedSuccess =
+            httpClient_.connect("localhost", httpServer_.port(), yield, std::chrono::milliseconds{100});
+        [&]() { ASSERT_TRUE(expectedSuccess.has_value()) << expectedSuccess.error().message(); }();
     });
 
     runSpawn([this](boost::asio::yield_context yield) {
@@ -391,8 +402,9 @@ TEST_F(HttpConnectionTests, isAdminSetAdmin)
     EXPECT_CALL(adminSetter, Call).WillOnce(testing::Return(true));
 
     util::spawn(ctx_, [this](boost::asio::yield_context yield) mutable {
-        auto maybeError = httpClient_.connect("localhost", httpServer_.port(), yield, std::chrono::milliseconds{100});
-        [&]() { ASSERT_FALSE(maybeError.has_value()) << maybeError->message(); }();
+        auto expectedSuccess =
+            httpClient_.connect("localhost", httpServer_.port(), yield, std::chrono::milliseconds{100});
+        [&]() { ASSERT_TRUE(expectedSuccess.has_value()) << expectedSuccess.error().message(); }();
     });
 
     runSpawn([&](boost::asio::yield_context yield) {
diff --git a/tests/unit/web/ng/impl/WsConnectionTests.cpp b/tests/unit/web/ng/impl/WsConnectionTests.cpp
index b66d8343..23959001 100644
--- a/tests/unit/web/ng/impl/WsConnectionTests.cpp
+++ b/tests/unit/web/ng/impl/WsConnectionTests.cpp
@@ -99,8 +99,9 @@ protected:
 TEST_F(WebWsConnectionTests, WasUpgraded)
 {
     util::spawn(ctx_, [this](boost::asio::yield_context yield) {
-        auto maybeError = wsClient_.connect("localhost", httpServer_.port(), yield, std::chrono::milliseconds{100});
-        [&]() { ASSERT_FALSE(maybeError.has_value()) << maybeError.value().message(); }();
+        auto expectedSuccess =
+            wsClient_.connect("localhost", httpServer_.port(), yield, std::chrono::milliseconds{100});
+        [&]() { ASSERT_TRUE(expectedSuccess.has_value()) << expectedSuccess.error().message(); }();
     });
     runSpawn([this](boost::asio::yield_context yield) {
         auto wsConnection = acceptConnection(yield);
@@ -115,8 +116,9 @@ TEST_F(WebWsConnectionTests, DisconnectClientOnInactivity)
     std::thread clientThread{[&clientCtx]() { clientCtx.run(); }};
 
     util::spawn(clientCtx, [&work, this](boost::asio::yield_context yield) {
-        auto maybeError = wsClient_.connect("localhost", httpServer_.port(), yield, std::chrono::milliseconds{100});
-        [&]() { ASSERT_FALSE(maybeError.has_value()) << maybeError.value().message(); }();
+        auto expectedSuccess =
+            wsClient_.connect("localhost", httpServer_.port(), yield, std::chrono::milliseconds{100});
+        [&]() { ASSERT_TRUE(expectedSuccess.has_value()) << expectedSuccess.error().message(); }();
         boost::asio::steady_timer timer{yield.get_executor(), std::chrono::milliseconds{5}};
         timer.async_wait(yield);
         work.reset();
@@ -143,8 +145,9 @@ TEST_F(WebWsConnectionTests, Send)
     Response const response{boost::beast::http::status::ok, "some response", request_};
 
     util::spawn(ctx_, [this, &response](boost::asio::yield_context yield) {
-        auto maybeError = wsClient_.connect("localhost", httpServer_.port(), yield, std::chrono::milliseconds{100});
-        [&]() { ASSERT_FALSE(maybeError.has_value()) << maybeError.value().message(); }();
+        auto expectedSuccess =
+            wsClient_.connect("localhost", httpServer_.port(), yield, std::chrono::milliseconds{100});
+        [&]() { ASSERT_TRUE(expectedSuccess.has_value()) << expectedSuccess.error().message(); }();
         auto const expectedMessage = wsClient_.receive(yield, std::chrono::milliseconds{100});
         [&]() { ASSERT_TRUE(expectedMessage.has_value()) << expectedMessage.error().message(); }();
         EXPECT_EQ(expectedMessage.value(), response.message());
@@ -152,8 +155,8 @@ TEST_F(WebWsConnectionTests, Send)
 
     runSpawn([this, &response](boost::asio::yield_context yield) {
         auto wsConnection = acceptConnection(yield);
-        auto maybeError = wsConnection->send(response, yield);
-        [&]() { ASSERT_FALSE(maybeError.has_value()) << maybeError.value().message(); }();
+        auto expectedSuccess = wsConnection->send(response, yield);
+        [&]() { ASSERT_TRUE(expectedSuccess.has_value()) << expectedSuccess.error().message(); }();
     });
 }
 
@@ -162,8 +165,9 @@ TEST_F(WebWsConnectionTests, SendShared)
     auto const response = std::make_shared<std::string>("some response");
 
     util::spawn(ctx_, [this, &response](boost::asio::yield_context yield) {
-        auto maybeError = wsClient_.connect("localhost", httpServer_.port(), yield, std::chrono::milliseconds{100});
-        [&]() { ASSERT_FALSE(maybeError.has_value()) << maybeError.value().message(); }();
+        auto expectedSuccess =
+            wsClient_.connect("localhost", httpServer_.port(), yield, std::chrono::milliseconds{100});
+        [&]() { ASSERT_TRUE(expectedSuccess.has_value()) << expectedSuccess.error().message(); }();
         auto const expectedMessage = wsClient_.receive(yield, std::chrono::milliseconds{100});
         [&]() { ASSERT_TRUE(expectedMessage.has_value()) << expectedMessage.error().message(); }();
         EXPECT_EQ(expectedMessage.value(), *response);
@@ -171,8 +175,8 @@ TEST_F(WebWsConnectionTests, SendShared)
 
     runSpawn([this, &response](boost::asio::yield_context yield) {
         auto wsConnection = acceptConnection(yield);
-        auto maybeError = wsConnection->sendShared(response, yield);
-        [&]() { ASSERT_FALSE(maybeError.has_value()) << maybeError.value().message(); }();
+        auto expectedSuccess = wsConnection->sendShared(response, yield);
+        [&]() { ASSERT_TRUE(expectedSuccess.has_value()) << expectedSuccess.error().message(); }();
     });
 }
 
@@ -181,8 +185,9 @@ TEST_F(WebWsConnectionTests, MultipleSend)
     Response const response{boost::beast::http::status::ok, "some response", request_};
 
     util::spawn(ctx_, [this, &response](boost::asio::yield_context yield) {
-        auto maybeError = wsClient_.connect("localhost", httpServer_.port(), yield, std::chrono::milliseconds{100});
-        [&]() { ASSERT_FALSE(maybeError.has_value()) << maybeError.value().message(); }();
+        auto expectedSuccess =
+            wsClient_.connect("localhost", httpServer_.port(), yield, std::chrono::milliseconds{100});
+        [&]() { ASSERT_TRUE(expectedSuccess.has_value()) << expectedSuccess.error().message(); }();
 
         for ([[maybe_unused]] auto i : std::ranges::iota_view{0, 3}) {
             auto const expectedMessage = wsClient_.receive(yield, std::chrono::milliseconds{100});
@@ -195,8 +200,8 @@ TEST_F(WebWsConnectionTests, MultipleSend)
         auto wsConnection = acceptConnection(yield);
 
         for ([[maybe_unused]] auto i : std::ranges::iota_view{0, 3}) {
-            auto maybeError = wsConnection->send(response, yield);
-            [&]() { ASSERT_FALSE(maybeError.has_value()) << maybeError.value().message(); }();
+            auto expectedSuccess = wsConnection->send(response, yield);
+            [&]() { ASSERT_TRUE(expectedSuccess.has_value()) << expectedSuccess.error().message(); }();
         }
     });
 }
@@ -206,8 +211,9 @@ TEST_F(WebWsConnectionTests, MultipleSendFromMultipleCoroutines)
     Response const response{boost::beast::http::status::ok, "some response", request_};
 
     util::spawn(ctx_, [this, &response](boost::asio::yield_context yield) {
-        auto maybeError = wsClient_.connect("localhost", httpServer_.port(), yield, std::chrono::milliseconds{100});
-        [&]() { ASSERT_FALSE(maybeError.has_value()) << maybeError.value().message(); }();
+        auto expectedSuccess =
+            wsClient_.connect("localhost", httpServer_.port(), yield, std::chrono::milliseconds{100});
+        [&]() { ASSERT_TRUE(expectedSuccess.has_value()) << expectedSuccess.error().message(); }();
 
         for ([[maybe_unused]] auto i : std::ranges::iota_view{0, 3}) {
             auto const expectedMessage = wsClient_.receive(yield, std::chrono::milliseconds{100});
@@ -222,8 +228,8 @@ TEST_F(WebWsConnectionTests, MultipleSendFromMultipleCoroutines)
         util::CoroutineGroup group{yield};
         for ([[maybe_unused]] auto i : std::ranges::iota_view{0, 3}) {
             group.spawn(yield, [&wsConnection, &response](boost::asio::yield_context innerYield) {
-                auto maybeError = wsConnection->send(response, innerYield);
-                [&]() { ASSERT_FALSE(maybeError.has_value()) << maybeError.value().message(); }();
+                auto expectedSuccess = wsConnection->send(response, innerYield);
+                [&]() { ASSERT_TRUE(expectedSuccess.has_value()) << expectedSuccess.error().message(); }();
             });
         }
         group.asyncWait(yield);
@@ -235,21 +241,22 @@ TEST_F(WebWsConnectionTests, SendFailed)
     Response const response{boost::beast::http::status::ok, "some response", request_};
 
     util::spawn(ctx_, [this](boost::asio::yield_context yield) {
-        auto maybeError = wsClient_.connect("localhost", httpServer_.port(), yield, std::chrono::milliseconds{100});
-        [&]() { ASSERT_FALSE(maybeError.has_value()) << maybeError.value().message(); }();
+        auto expectedSuccess =
+            wsClient_.connect("localhost", httpServer_.port(), yield, std::chrono::milliseconds{100});
+        [&]() { ASSERT_TRUE(expectedSuccess.has_value()) << expectedSuccess.error().message(); }();
         wsClient_.close();
     });
 
     runSpawn([this, &response](boost::asio::yield_context yield) {
         auto wsConnection = acceptConnection(yield);
         wsConnection->setTimeout(std::chrono::milliseconds{1});
-        std::optional<Error> maybeError;
+        std::expected<void, Error> expectedSuccess;
         size_t counter = 0;
-        while (not maybeError.has_value() and counter < 100) {
-            maybeError = wsConnection->send(response, yield);
+        while (expectedSuccess.has_value() and counter < 100) {
+            expectedSuccess = wsConnection->send(response, yield);
             ++counter;
         }
-        EXPECT_TRUE(maybeError.has_value());
+        EXPECT_FALSE(expectedSuccess.has_value());
         EXPECT_LT(counter, 100);
     });
 }
@@ -259,8 +266,9 @@ TEST_F(WebWsConnectionTests, SendFailedSendingFromMultipleCoroutines)
     Response const response{boost::beast::http::status::ok, "some response", request_};
 
     util::spawn(ctx_, [this, &response](boost::asio::yield_context yield) {
-        auto maybeError = wsClient_.connect("localhost", httpServer_.port(), yield, std::chrono::milliseconds{100});
-        [&]() { ASSERT_FALSE(maybeError.has_value()) << maybeError.value().message(); }();
+        auto expectedSuccess =
+            wsClient_.connect("localhost", httpServer_.port(), yield, std::chrono::milliseconds{100});
+        [&]() { ASSERT_TRUE(expectedSuccess.has_value()) << expectedSuccess.error().message(); }();
 
         auto const expectedMessage = wsClient_.receive(yield, std::chrono::milliseconds{100});
         [&]() { ASSERT_TRUE(expectedMessage.has_value()) << expectedMessage.error().message(); }();
@@ -271,15 +279,15 @@ TEST_F(WebWsConnectionTests, SendFailedSendingFromMultipleCoroutines)
     runSpawn([this, &response](boost::asio::yield_context yield) {
         auto wsConnection = acceptConnection(yield);
         wsConnection->setTimeout(std::chrono::milliseconds{1});
-        std::optional<Error> maybeError;
+        std::expected<void, Error> expectedSuccess;
         size_t counter = 0;
-        while (not maybeError.has_value() and counter < 100) {
-            maybeError = wsConnection->send(response, yield);
+        while (expectedSuccess.has_value() and counter < 100) {
+            expectedSuccess = wsConnection->send(response, yield);
             ++counter;
         }
         // Sending after getting an error should be safe
-        maybeError = wsConnection->send(response, yield);
-        EXPECT_TRUE(maybeError.has_value());
+        expectedSuccess = wsConnection->send(response, yield);
+        EXPECT_FALSE(expectedSuccess.has_value());
         EXPECT_LT(counter, 100);
     });
 }
@@ -287,11 +295,12 @@ TEST_F(WebWsConnectionTests, SendFailedSendingFromMultipleCoroutines)
 TEST_F(WebWsConnectionTests, Receive)
 {
     util::spawn(ctx_, [this](boost::asio::yield_context yield) {
-        auto maybeError = wsClient_.connect("localhost", httpServer_.port(), yield, std::chrono::milliseconds{100});
-        [&]() { ASSERT_FALSE(maybeError.has_value()) << maybeError.value().message(); }();
+        auto expectedSuccess =
+            wsClient_.connect("localhost", httpServer_.port(), yield, std::chrono::milliseconds{100});
+        [&]() { ASSERT_TRUE(expectedSuccess.has_value()) << expectedSuccess.error().message(); }();
 
-        maybeError = wsClient_.send(yield, request_.message(), std::chrono::milliseconds{100});
-        EXPECT_FALSE(maybeError.has_value()) << maybeError->message();
+        expectedSuccess = wsClient_.send(yield, request_.message(), std::chrono::milliseconds{100});
+        EXPECT_TRUE(expectedSuccess.has_value()) << expectedSuccess.error().message();
     });
 
     runSpawn([this](boost::asio::yield_context yield) {
@@ -306,12 +315,13 @@ TEST_F(WebWsConnectionTests, Receive)
 TEST_F(WebWsConnectionTests, MultipleReceive)
 {
     util::spawn(ctx_, [this](boost::asio::yield_context yield) {
-        auto maybeError = wsClient_.connect("localhost", httpServer_.port(), yield, std::chrono::milliseconds{100});
-        [&]() { ASSERT_FALSE(maybeError.has_value()) << maybeError.value().message(); }();
+        auto expectedSuccess =
+            wsClient_.connect("localhost", httpServer_.port(), yield, std::chrono::milliseconds{100});
+        [&]() { ASSERT_TRUE(expectedSuccess.has_value()) << expectedSuccess.error().message(); }();
 
         for ([[maybe_unused]] auto i : std::ranges::iota_view{0, 3}) {
-            maybeError = wsClient_.send(yield, request_.message(), std::chrono::milliseconds{100});
-            EXPECT_FALSE(maybeError.has_value()) << maybeError->message();
+            expectedSuccess = wsClient_.send(yield, request_.message(), std::chrono::milliseconds{100});
+            EXPECT_TRUE(expectedSuccess.has_value()) << expectedSuccess.error().message();
         }
     });
 
@@ -329,8 +339,9 @@ TEST_F(WebWsConnectionTests, MultipleReceive)
 TEST_F(WebWsConnectionTests, ReceiveTimeout)
 {
     util::spawn(ctx_, [this](boost::asio::yield_context yield) {
-        auto maybeError = wsClient_.connect("localhost", httpServer_.port(), yield, std::chrono::milliseconds{100});
-        [&]() { ASSERT_FALSE(maybeError.has_value()) << maybeError.value().message(); }();
+        auto expectedSuccess =
+            wsClient_.connect("localhost", httpServer_.port(), yield, std::chrono::milliseconds{100});
+        [&]() { ASSERT_TRUE(expectedSuccess.has_value()) << expectedSuccess.error().message(); }();
     });
 
     runSpawn([this](boost::asio::yield_context yield) {
@@ -345,8 +356,9 @@ TEST_F(WebWsConnectionTests, ReceiveTimeout)
 TEST_F(WebWsConnectionTests, ReceiveFailed)
 {
     util::spawn(ctx_, [this](boost::asio::yield_context yield) {
-        auto maybeError = wsClient_.connect("localhost", httpServer_.port(), yield, std::chrono::milliseconds{100});
-        [&]() { ASSERT_FALSE(maybeError.has_value()) << maybeError.value().message(); }();
+        auto expectedSuccess =
+            wsClient_.connect("localhost", httpServer_.port(), yield, std::chrono::milliseconds{100});
+        [&]() { ASSERT_TRUE(expectedSuccess.has_value()) << expectedSuccess.error().message(); }();
         wsClient_.close();
     });
 
@@ -361,8 +373,9 @@ TEST_F(WebWsConnectionTests, ReceiveFailed)
 TEST_F(WebWsConnectionTests, Close)
 {
     util::spawn(ctx_, [this](boost::asio::yield_context yield) {
-        auto maybeError = wsClient_.connect("localhost", httpServer_.port(), yield, std::chrono::milliseconds{100});
-        [&]() { ASSERT_FALSE(maybeError.has_value()) << maybeError.value().message(); }();
+        auto expectedSuccess =
+            wsClient_.connect("localhost", httpServer_.port(), yield, std::chrono::milliseconds{100});
+        [&]() { ASSERT_TRUE(expectedSuccess.has_value()) << expectedSuccess.error().message(); }();
         auto const maybeMessage = wsClient_.receive(yield, std::chrono::milliseconds{100});
         EXPECT_FALSE(maybeMessage.has_value());
         EXPECT_THAT(maybeMessage.error().message(), testing::HasSubstr("was gracefully closed"));
@@ -377,8 +390,9 @@ TEST_F(WebWsConnectionTests, Close)
 TEST_F(WebWsConnectionTests, CloseWhenConnectionIsAlreadyClosed)
 {
     util::spawn(ctx_, [this](boost::asio::yield_context yield) {
-        auto maybeError = wsClient_.connect("localhost", httpServer_.port(), yield, std::chrono::milliseconds{100});
-        [&]() { ASSERT_FALSE(maybeError.has_value()) << maybeError.value().message(); }();
+        auto expectedSuccess =
+            wsClient_.connect("localhost", httpServer_.port(), yield, std::chrono::milliseconds{100});
+        [&]() { ASSERT_TRUE(expectedSuccess.has_value()) << expectedSuccess.error().message(); }();
         wsClient_.close();
     });
 
@@ -393,8 +407,9 @@ TEST_F(WebWsConnectionTests, CloseWhenConnectionIsAlreadyClosed)
 TEST_F(WebWsConnectionTests, CloseCalledFromMultipleSubCoroutines)
 {
     util::spawn(ctx_, [this](boost::asio::yield_context yield) {
-        auto maybeError = wsClient_.connect("localhost", httpServer_.port(), yield, std::chrono::milliseconds{100});
-        [&]() { ASSERT_FALSE(maybeError.has_value()) << maybeError.value().message(); }();
+        auto expectedSuccess =
+            wsClient_.connect("localhost", httpServer_.port(), yield, std::chrono::milliseconds{100});
+        [&]() { ASSERT_TRUE(expectedSuccess.has_value()) << expectedSuccess.error().message(); }();
     });
 
     testing::StrictMock<testing::MockFunction<void()>> closeCalled;